A few weeks ago I hiked the Enchantments here in Washington State — one of the most beautiful trails in the country, and one of the most punishing. Going up Aasgard Pass, you climb nearly 5,000 feet to almost 8,000 feet above sea level. More than once, I caught myself wondering whether I was even on the right trail. The path would vanish into rock fields or under late-season snow, and I'd have to stop, backtrack, and search for a cairn or another hiker. What struck me afterward was how familiar that feeling was. It's the same feeling investors know well: the right path almost never feels obvious while you're walking it.
In this week's video, I walk through three moments where a good investment decision feels completely wrong. Buying when markets are falling and the news is grim. Holding when markets are at all-time highs and every expert on TV says take profits. And selling when a long trend finally turns, even though every instinct says the dip will bounce like all the others did. In each case, the discomfort isn't a warning sign — it's often the price of admission. I'll be honest: I've thought U.S. stocks looked expensive for a while now. If I had acted on that opinion, I would have missed significant gains. That's exactly why I follow a disciplined process instead of my gut. My opinions can be wrong; my process keeps me on the trail.
On the hike, I rarely had certainty about the next hundred feet — but I knew I was generally moving in the right direction, so I kept going. Investing works the same way. Successful investors don't have more certainty than everyone else; they have a process they're willing to trust when uncertainty shows up. Because in investing, discipline is more profitable than comfort. If you'd like to talk about what a disciplined process could look like for your own portfolio, I'd welcome the conversation.
